DOI: 10.1002/open.

201900001

Designing Self-Assembled Rosettes: Why Ammeline is a

Superior Building Block to Melamine

Andr Nicolai Petelski Clia Fonseca Guerra

Invited for this month’s cover picture are Professor Clia Fonseca Guerra from Vrije Universiteit Amsterdam and Leiden Uni-
versity (The Netherlands) and Andr Nicolai Petelski from UTN-FRRe University of Argentine (Argentina). The cover picture
shows a colored pallet of melamine and ammeline tautomers that form hydrogen-bonded hexameric rosettes. When it
comes to self-assembling capabilities, one of the ammeline structures (red) is shown to be distinctly superior to melamine,
both in the gas phase and in water. Quantum chemical computations explain that this is due to the presence of stronger
pair interactions and the manifestation of a large cooperativity effect. Read the full text of their Full Paper at 10.1002/
open.201800210.

What is the most significant result of this study? Is your current research mainly curiosity driven
Melamine is an amino triazine that is extensively used in supra- (fundamental) or rather applied?
molecular chemistry. We have found that its first hydrolysis by- Our research on chemical bonding is driven by our curiosity to
product, which is called ammeline, shows a better self-assem- obtain fundamental insight into the chemistry of how materi-
bling capability than melamine. Through quantum chemical als form. At the same time, our newly obtained understanding
bonding analysis, we prove that ammeline has stronger pair in- finds its way into applications by giving more reliable predic-
teractions than melamine, not only in the gas phase but even tions for self-assembly and reactivity.
in water. In addition, ammeline displays an exceptional phe-
nomenon, which is of great importance in supramolecular
chemistry: a cooperativity effect in hydrogen bonding. These
two features can be exploited by experimentalists in their
quest for more efficient supramolecular materials.

Who designed the cover?

The cover was designed by Andr Nicolai Petelski with the col-
laborations of graphic designer Alexandra Lena Petelski and
Professor Clia Fonseca Guerra. The cover is a representation
of computer-aided design of supramolecular systems. A col-
ored pallet of molecular structures is deeply analyzed by a set
of computational screening tests, so that the hydrogen-
bonded rosette with the best properties is chosen.

How did the collaboration on this project start?

This project started at a scientific meeting of computational
and theoretical chemists (QUITEL 2016). As we are both inter-
ested in cooperativity in hydrogen bonding, we applied Kohn–
Sham molecular orbital theory to the hydrogen bonds of mela-
mine and ammeline rosettes. The collaboration has evolved
into a double degree PhD for Andr Nicolai Petelski at Vrije
Universiteit Amsterdam and Universidad Tecnolgica Nacional,
Resistencia.

ChemistryOpen 2018, 00, 0 – 0 1  2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim &

These are not the final page numbers! ÞÞ

 COVER PROFILE
A. N. Petelski, C. Fonseca Guerra* “Hydrogen-bonded rosettes of melamine
are widely used in supramolecular
&& – &&
chemistry. However, computational ex-
Designing Self-Assembled Rosettes: periments suggest that ammeline is a
Why Ammeline is a Superior Building more robust building block for fabricating
Block to Melamine these cyclic complexes...”
Find out more about the story behind
the front cover research at 10.1002/
open.201800210.

& ChemistryOpen 2018, 00, 0 – 0 www.chemistryopen.org 2  2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

ÝÝ These are not the final page numbers!